Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles

• Main Author: Dang, Jeremy
• Other Authors: Georges, Michael
• Language: en_ca
• Published: 2010
• Subjects: Verdazyl radicals; 1,3-dipolar cycloaddition; azomethine imine; heterocyclic syntheses; pyrazolotetrazinanone; 0490
• Online Access: http://hdl.handle.net/1807/29984

The emergence of verdazyl radicals as starting materials for organic synthesis is providing a unique opportunity to create a variety of distinctive heterocyclic scaffolds. These stable radicals have previously been used as spin probes, polymerization inhibitors, mediators of living radical polymerizations, and as substrates for molecular-based magnets. However, verdazyl radicals have never been employed to fulfill an organic synthetic role until recently. In an effort to pioneer the chemistry behind verdazyl radicals as novel organic substrates, our lab has been inspired to expand and explore the scope of reactions involving their synthetic utility. This thesis assesses the synthetic versatility of verdazyl radicals by constructing a library of structurally complex and diverse verdazyl-derived heterocycles in an approach called diversity-oriented synthesis. The synthetic versatility was further expanded to the preparation of a biphenyl-stacked biphenylophane, which exhibited interesting structural and conformational features as highlighted herein.